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Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines

Wubing Yao*, Lili He, Deman Han and Aiguo Zhong

*School of Pharmaceutical and Materials Engineering, Taizhou University, Jiaojiang 318000, Zhejiang, China, Email: icyyw2010yeah.net

W. Yao, L. He, D. Han, A. Zhong, J. Org. Chem., 2019, 84, 14627-14635.

DOI: 10.1021/acs.joc.9b02211 (free Supporting Information)


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Abstract

Transition-metal-free catalytic protocols for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents enable the selective reduction of unactivated C-O bonds in amides. By altering the hydrosilane and solvent, the C-N bonds selectively breaks via a deacylative cleavage.

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Key Words

reduction of amides, acetamides, deacylation, triethoxysilane, PMHS


ID: J42-Y2019